Methyl 2-fluoro-4-nitrobenzoate → Methyl 4-amino-2-fluorobenzoate

HRID 1843034Notes

Reaction equation

HRID 1843034 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[NH2:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1

Participants

4

Reactant 1

HCID 3013872Methyl 2-fluoro-4-nitrobenzoate

Product 1

HCID 21957875Methyl 4-amino-2-fluorobenzoateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-fluoro-4-nitrobenzoate (1.05 g, 5.273 mmol) was dissolved in MeOH. Pd/C (105 mg) was added to the resulting mixture. The reaction mixture was stirred at room temperature for 2 hours under H2. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography to give pure compound methyl 4-amino-2-fluorobenzoate (870 mg, 98%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-56b6c34ab3724002b69f4fbd7604031a
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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